US9296675B2 - Compound having cyclopropane ring, and flavor and/or fragrance composition containing same - Google Patents

Compound having cyclopropane ring, and flavor and/or fragrance composition containing same Download PDF

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US9296675B2
US9296675B2 US14/760,744 US201414760744A US9296675B2 US 9296675 B2 US9296675 B2 US 9296675B2 US 201414760744 A US201414760744 A US 201414760744A US 9296675 B2 US9296675 B2 US 9296675B2
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Kenichi Yamamoto
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Takasago International Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/293—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with three- or four-membered ring
    • A23L1/2265—
    • A23L1/22657—
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • C07C2101/02—
    • C07C2101/16—
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to a flavor and/or fragrance composition containing a compound having a cyclopropane ring.
  • Some compounds having a cyclopropane ring are known to be useful as raw materials for flavor compositions and/or fragrance compositions.
  • [1-methyl-2-(5-methyl-4-hexen-2-yl)cyclopropyl]methanol has an odor similar to those of citrus and 3-methyl-5-phenyl-1-pentanol, with rosy floral note (WO 2012/160189 A1).
  • 1-methyl-2-[(2,2,3-trimethylcyclopentyl)methyl]cyclopropyl]methanol has a natural sandalwood-like odor (US 2010/0069508 A1).
  • 2-(1-phenylethyl)cyclopropylmethanol and the like are known as compounds having a cyclopropane ring and a benzene ring, but their odors are not mentioned (Synthesis (1999), No. 6, 1063-1075).
  • an object of the present invention is to provide a compound capable of imparting a floral or citrus-like odor satisfying the above-described requirements.
  • the present invention includes the following contents [1] to [7].
  • R 1 , R 2 , R 3 , and R 5 each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that two or more groups of R 1 , R 2 , R 3 , and R 5 are alkyl groups;
  • R 4 represents a group selected from a formyl group, a hydroxymethyl group, a 1-hydroxy-1-ethyl group, a 1-hydroxy-1-propyl group, a 1-hydroxy-1-butyl group, and a 2-hydroxy-1-propyl group;
  • n 0 to 2;
  • n 0 or 1
  • the wavy lines indicate a cis-configuration, a trans-configuration, or a mixture of a cis-configuration and a trans-configuration with respect to position-2 on the cyclopropane ring.
  • R 4 is a group selected from a hydroxymethyl group, a 1-hydroxy-1-ethyl group, a 1-hydroxy-1-propyl group, a 1-hydroxy-1-butyl group, and a 2-hydroxy-1-propyl group.
  • R 1 and R 3 are both methyl groups.
  • R 1 , R 2 , and R 3 are all methyl groups.
  • R 5 is a methyl group.
  • the compound of the present invention is a very useful flavor and/or fragrance material which is highly preferred, is also excellent in odor-imparting characteristics, and is excellent in diffusibility and long lasting.
  • an agent for imparting a highly preferred odor can be provided.
  • a compound of the present invention is represented by Formula (1):
  • R 1 , R 2 , R 3 , and R 5 each represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that two or more groups of R 1 , R 2 , R 3 , and R 5 are alkyl groups.
  • the alkyl group having 1 to 3 carbon atoms is, for example, a methyl group.
  • R 4 represents a group selected from a formyl group, a hydroxymethyl group, a 1-hydroxy-1-ethyl group, a 1-hydroxy-1-propyl group, a 1-hydroxy-1-butyl group, and a 2-hydroxy-1-propyl group.
  • R 4 is, for example, selected from a formyl group, a hydroxymethyl group, and a 1-hydroxy-1-ethyl group.
  • m is 0 to 2, and, for example, 0 or 1.
  • n is 0 or 1.
  • the wavy lines indicate a cis-configuration, a trans-configuration, or a mixture of a cis-configuration and a trans-configuration with respect to position-2 on the cyclopropane ring.
  • a compound of Formula (1), where n is 0, and R 4 is a hydroxymethyl group, is synthesized, for example, by a method shown below.
  • an allyl alcohol derivative (3) is reacted with a carbenoid prepared from diethylzinc and chloroiodomethane to synthesize a compound (4) having a cyclopropane ring.
  • the compound (4) having a cyclopropane ring is obtained as a mixture of diastereomers having the relative configurations shown below, and the odor threshold of (4b) is lower than that of (4a).
  • a compound of Formula (1), where n is 0, m is 0, R 1 and R 3 are methyl groups, and R 4 is a 1-hydroxy-1-ethyl group, is synthesized, for example, by a method shown below.
  • a compound (5) having a cyclopropane ring is oxidized to obtain an aldehyde compound (6), which is then subjected to a Grignard reaction.
  • a compound (7) can be synthesized.
  • Reactions usable as a method for the oxidation include the TEMPO oxidation, the Uemura Oxidation, the Albright-Goldman oxidation, the Mukaiyama oxidation, the Ley-Griffith oxidation, the Swern oxidation, and the like.
  • the compound (7) having a cyclopropane ring is obtained as a mixture of isomers having relative configurations shown below.
  • the odor threshold of (R*)-1-[(1S*,2S*)-1-methyl-2-((R*)-1-phenylethyl)cyclopropyl]ethanol (7a) is 100 times or more lower than that of (S*)-1-[(1S*,2S*)-1-methyl-2-((R*)-1-phenylethyl)cyclopropyl]ethanol (7b).
  • a compound having a cyclopropane ring of Formula (1), where n is 1, m is 0, R 1 and R 3 are methyl groups, and R 4 is a formyl group, is synthesized, for example, by a method shown below.
  • a compound (6) is subjected to the Wittig reaction to synthesize an enol ether (8).
  • the obtained enol ether is hydrolyzed in the presence of an acid catalyst.
  • an acid catalyst e.g., a compound (9) having a cyclopropane ring.
  • Acids used here include acetic acid, citric acid, hydrochloric acid, sulfuric acid, and the like.
  • the thus obtained compound of the present invention can be isolated and purified.
  • methods for the isolation and purification include column chromatography, vacuum distillation, crystallization, and the like. These methods can be carried out alone or in combination.
  • the amount of the compound represented by Formula (1) blended in a flavor and/or fragrance composition is not particularly limited, and is preferably 0.01 to 60% by weight, and particularly preferably 0.1 to 40% by weight, relative to the flavor and/or fragrance composition.
  • any commonly used blended flavor and/or fragrance can be blended in the flavor and/or fragrance composition of the present invention.
  • the thus obtained flavor and/or fragrance composition can impart a fresh and highly preferred odor.
  • the flavor and/or fragrance composition of the present invention can be blended, as an odor component, in foods and beverages, cosmetics, air-fresheners, daily necessities and groceries, oral cavity compositions, hair-care products, skin-care products, body-cleaning agents, laundry detergents, laundry softeners, toiletry products, fibers and fiber products, garments, pharmaceuticals, and the like.
  • the flavor and/or fragrance composition of the present invention can be blended in shampoos, rinses, perfumes, colognes, hair tonics, hair creams, pomades, base materials for other hair cosmetics, soaps, dish washing detergents, laundry detergents, softeners, sterilizing detergents, deodorant detergents, room air-fresheners, disinfectants, pesticides, bleaching agents, other various health and sanitary detergents, dentifrices, mouthwashes, toilet papers, odor-imparting agents for facilitating ingestion of pharmaceuticals, and the like in amounts generally employed in these industrial fields. In this manner, its unique odor can be imparted to these products, and the values of the products can be enhanced.
  • GC/MS was measured by using an HP 6890 GC system and an HP5973MS detector of Agirent Technologies.
  • the column used was InertCap 1 (manufactured by GL Sciences Inc., 30 m in length ⁇ 0.25 mm in inner diameter, liquid-phase film thickness: 0.25 ⁇ m).
  • the injection port temperature was 250° C.
  • the detector temperature was 250° C.
  • the conditions of the temperature rise were as follows: 100° C. (15° C./minute) 300° C.
  • the GC purity was measured by using a 7890A GC system of Agirent Technologies.
  • the column used was InertCap 1 (manufactured by GL Sciences Inc., 20 m in length ⁇ 0.18 in mm inner diameter, liquid-phase film thickness: 0.18 ⁇ m).
  • the injection port temperature was 250° C.
  • the detector temperature was 250° C.
  • the conditions of the temperature rise were as follows: 100° C. (15° C./minute) 230° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 37.9 g, 46.0 mmol) was placed into a 200-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 20° C.
  • Chloroiodomethane (16.22 g, 92.0 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 to ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 15° C. for 30 minutes, and then cooled to ⁇ 25° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 69.8 g, 84.8 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 20° C.
  • Chloroiodomethane (29.9 g, 169.6 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 15° C. for 30 minutes, and then cooled to ⁇ 25° C.
  • methyl magnesium bromide (0.97 mol/L, tetrahydrofuran solution, 8.5 ml, 8.25 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 10° C.
  • (1S*,2S*)-1-Methyl-2-[(R*)-1-phenylethyl]cyclopropane carbaldehyde (1.03 g, 5.5 mmol) was placed into the dropping funnel, and added dropwise in 5 minutes with the temperature kept at ⁇ 10° C. After stirring for 60 minutes, a 20% aqueous sulfuric acid solution (4.5 g) was added.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 10.9 g, 13.2 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 15° C.
  • Chloroiodomethane (4.68 g, 26.5 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 15° C. for 30 minutes.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 5.3 g, 6.4 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 20° C.
  • Chloroiodomethane (2.26 g, 12.8 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 15° C. for 10 minutes, and then cooled to ⁇ 20° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 9.4 g, 11.4 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 15° C.
  • Chloroiodomethane (4.02 g, 22.8 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept at ⁇ 15° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 15° C. for 20 minutes, and then cooled to ⁇ 25° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 6.92 g, 8.4 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 25° C.
  • Chloroiodomethane (2.96 g, 16.8 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 20 and ⁇ 25° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 20° C. for 15 minutes, and then cooled to ⁇ 25° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 9.4 g, 0.0114 mol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 15° C.
  • Chloroiodomethane (4.02 g, 22.8 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 10 to ⁇ 15° C. for 20 minutes, and then cooled to ⁇ 25° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 6.92 g, 8.4 mmol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 20° C.
  • Chloroiodomethane (2.96 g, 16.8 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 5 to ⁇ 15° C. for 10 minutes, and then cooled to ⁇ 25° C.
  • a diethylzinc solution in toluene (concentration: 15% by weight, 5.4 g, 0.0066 mol) was placed into a 100-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer, and cooled to ⁇ 20° C.
  • Chloroiodomethane (2.33 g, 13.2 mmol) was placed into the dropping funnel, and added dropwise with the temperature kept between ⁇ 15 and ⁇ 20° C. After completion of the dropwise addition, the mixture was stirred at ⁇ 5 to ⁇ 15° C. for 20 minutes, and then cooled to ⁇ 25° C.
  • methyl magnesium bromide (0.97 mol/L tetrahydrofuran solution, 3.0 ml, 2.9 mmol) was placed into a 30-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer.
  • 2-[(1R*,2S*)-1-methyl-2-(1-phenylethyl)cyclopropyl]acetaldehyde (a diastereomer mixture with a component ratio of 1:2, 0.20 g, 0.99 mmol) and tetrahydrofuran (1 ml) were placed, and added dropwise in 5 minutes, with the temperature kept at 20° C. At the same temperature, the mixture was stirred for 30 minutes.
  • Flavor and/or fragrance compositions for perfume were prepared according to the formulation shown in Table 4 below by using the compounds synthesized in Examples 1, 2, 4, 8, 9, and 10 described above.
  • Flavor and/or fragrance compositions for perfume were prepared according to the formulation shown in Table 5 below by using the compounds of Examples 1, 2, 4, 8, 9, and 10.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Seasonings (AREA)
US14/760,744 2013-03-12 2014-03-07 Compound having cyclopropane ring, and flavor and/or fragrance composition containing same Active US9296675B2 (en)

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JP2013048678 2013-03-12
JP2013-048678 2013-03-12
PCT/JP2014/055956 WO2014142025A1 (fr) 2013-03-12 2014-03-07 Composé ayant un cycle cyclopropane, et composition d'arôme le contenant

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862340A (en) 1972-08-25 1975-01-21 Int Flavors & Fragrances Inc Flavoring with 5-phenyl pentenals
JPS63183522A (ja) 1986-09-08 1988-07-28 Kuraray Co Ltd 香料組成物
JPS63227546A (ja) 1987-03-17 1988-09-21 Kuraray Co Ltd 第１級アリルエステルの製造方法
US20050119156A1 (en) 2001-12-19 2005-06-02 Luca Turin Aromachemicals
JP2006506316A (ja) 2001-12-19 2006-02-23 フレキシトラル・インコーポレイテツド 改良された芳香薬品
US20100069508A1 (en) 2006-11-03 2010-03-18 Givaudan Sa Organic Compounds
WO2011051834A1 (fr) 2009-11-02 2011-05-05 Firmenich Sa Substances odorantes ayant des notes anisiques
WO2012160189A1 (fr) 2011-05-25 2012-11-29 Givaudan Sa Alcools terpéniques destinés à être utilisés dans des compositions de parfum et produits parfumés

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3948973A (en) * 1972-08-29 1976-04-06 Sterling Drug Inc. Halocyclopropyl substituted phenoxyalkanoic acids
GB0716232D0 (en) * 2007-08-21 2007-09-26 Givaudan Sa Cyclopropanation process
WO2010065446A2 (fr) * 2008-12-01 2010-06-10 The Procter & Gamble Company Systèmes parfumeurs

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862340A (en) 1972-08-25 1975-01-21 Int Flavors & Fragrances Inc Flavoring with 5-phenyl pentenals
JPS63183522A (ja) 1986-09-08 1988-07-28 Kuraray Co Ltd 香料組成物
JPS63227546A (ja) 1987-03-17 1988-09-21 Kuraray Co Ltd 第１級アリルエステルの製造方法
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JPWO2014142025A1 (ja) 2017-02-16
US20150353461A1 (en) 2015-12-10
CN105073698B (zh) 2017-03-15
EP2985273A4 (fr) 2016-07-13
EP2985273B1 (fr) 2018-07-04
WO2014142025A1 (fr) 2014-09-18
EP2985273A1 (fr) 2016-02-17

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